


Cry Little Sister

by dollylux



Category: Supernatural
Genre: Consensual Underage Sex, Crossdressing, Crossdressing Sam, Dirty Talk, Genderplay, Grinding, M/M, Roleplay
Language: English
Status: Completed
Published: 2014-10-25
Updated: 2014-10-25
Packaged: 2018-02-22 13:49:19
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,235
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2510024
Author URL: https://archiveofourown.org/users/dollylux/pseuds/dollylux
Summary: <blockquote class="userstuff">
              <p>Sam wants Dean to play with him.</p>
            </blockquote>





	Cry Little Sister

**Author's Note:**

  * For [LibraOnFire](https://archiveofourown.org/users/LibraOnFire/gifts).



> Sam is fifteen, Dean is nineteen.
> 
> Happy birthday, Clare! :D

Sam had been thinking about it for months. And months are their own small eternities when you’re fifteen.

He’s sure something fucked-up started it, like seeing some older brother being protective of his sister at some school between here and wherever the fuck, or some fever dream in which he had distinctly felt the fall of a skirt over his skinny legs and all the bareness that comes with it.

Well. Whatever it was, here he is. With these increasingly bizarre thoughts, even from someone who sucks his brother’s dick on the regular, obsessed with something he wants so bad he doesn’t even know how to ask Dean about it. How to ask Dean _for_ it.

Fifteen year olds, along with being dramatic, also aren’t very good at subtlety.

 

  
“What would you think if I wore a skirt?”

Maybe not the best question to ask when Dean’s driving, because Dean swerves on the road, car jerking hard to the left before Dean rights it, his hands in a deathgrip on the wheel.

Sam squirms in his seat.

“Or maybe just, like, cut-offs?”

“Sammy, what the fuck?” Dean’s frowning, in that I’m-turned-on-but-shouldn’t-be way, not in the annoyed way, and it’s a little bit of a relief when Dean reaches down between his own legs to adjust himself. “Why you askin’ me that?”

“Nothing it’s fine,” he rushes out, his cheeks flushed, but he’s got his answer, whether Dean meant to give it to him or not.

He starts to plan.

  
  
It goes down in Bitter Springs, Arizona in August, three days before school starts back up.

Dean’s in the livingroom of the little shack Dad had managed to stuff them in, watching the ancient, jumpy TV, some soap opera with a woman crying and a man drinking in a fancy room in some mansion. Sam watches him for a minute from the doorway, most of his body hidden in the dark hallway.

“Dean?”

Dean grunts a reply, but he doesn’t move or speak otherwise. Sam licks his lips, shifting one bare foot on top of the other as he gathers more courage.

“Can you close your eyes?”

Dean, of course, turns around immediately for that. “Huh?”

“Don’t!” Sam ducks back into the hallway, his cheeks burning hot with embarrassment. “Just. Just, _please_? Just for a minute? And turn the TV off?”

Dean looks away in a sudden fit of obedience, but the set of his shoulders tells Sam that he’s not exactly happy about this. It’s tense between them, quiet for a long moment before Dean sucks in a sudden breath, almost turning around again to face Sam but he resists.

“Wait. Is this a sex thing?”

Sam huffs, almost indignant before he realizes that it really kind of is, and then he’s smiling down at his bare, wriggling toes, shy about how well Dean knows him.

“Kinda.”

Dean relaxes back against the couch immediately, the TV flicking off as if by magic, and Sam can practically see his self-satisfied smirk.

“Got ‘em closed, Sammy.”

Okay, it’s time. It’s time. Just breathe. Don’t pass out while you’re wearing daisy dukes and Lipsmackers and pigtails. Just _breathe_.

He rounds the corner into the livingroom cautiously, like Dean’s a sleeping tiger, a boombox clutched in one hand, and a ratty old bandana in the other. He gets close enough to see that Dean is a horny teenager of his word and that his eyes are indeed closed.

Sam sets the boombox down near the couch and plugs it in, pushing play on the CD and hitting repeat. The song he’s been listening to in headphones while he jerks off for months now, fucking _months_ , starts up, “Cry Little Sister” from _The Lost Boys_ starts up, and it drives Pavlovian goosebumps up Sam’s spine immediately.

“Hey,” Dean mumbles, one of his hands already down between his legs, massaging, “idn’t this that song from _The Lost Boys_? When--”

“Dean?” Sam is standing over him now, bandana clutched in his hand, and he’s staring at his brother’s mouth, at his open, available lap, and all he can think about is getting every single bit of Dean on every single bit of him as soon as possible. Dean’s eyebrows draw together, and he lifts his head in the direction of Sam’s voice.

“Yeah?”

“Will you play with me?”

He lowers down onto Dean’s lap then, straddling him way too naturally, long newly-shaven, bare legs spread around Dean’s lean hips. Dean’s hands immediately come down to grip Sam’s legs, and the second he touches them, the slick nakedness of them, he gasps. Sam claps a hand over Dean’s eyes before they fly open, because he know they will. He curls down and presses his mouth to Dean’s ear, his entire face and chest flushed, voice coming out in a shy whisper.

“Can we play that I’m your little sister?”

“Fuck,” Dean grits out, big hands spreading out on Sam’s boy-scrawny thighs, thick fingers digging in almost hard enough to bruise. He nods behind Sam’s hand, tongue stealing out to lick over his plush mouth. “Yeah. Yeah, Sammy, we can do that.”

The song plays on nearby as Sam lifts up the bandana and wraps it around Dean’s eyes, leaning forward against him to tie it behind his head. Dean groans, his mouth momentarily against Sam’s throat, his hands sliding up Sam’s thighs and pushing up under his skimpy denim cut-offs.

“What’re you doin’, Sammy girl? What don’t you want me to see, hmm? Not gonna let your big brother see how pretty you look?”

Sam hums, pleased, because of course Dean is on board with this, will get off on this as much as Sam will. Because Dean’s just as fucked-up as he is. They’re fucked-up together.

He stretches out long as a cat over top of Dean, back arching as Dean’s hands make their way up his back, thumbs sliding over the barely-there curve of his hips and the narrowness of his waist.

“You wanna see me?”

Dean’s dick fattens underneath him, thickens right up under the tight plush of Sam’s ass, and Sam makes sure to grind right down against it, to give Dean something to fuck against.

_Cry little sister - thou shall not fall_

_Come to your brother - thou shall not die_

“You dressed up for me, little sister? Get all pretty for me?”

_Unchain me, sister - thou shall not fear_

_Love is with your brother - thou shall not kill_

“Yeah,” Sam breathes, writhing against Dean’s hands that are worshipping him thanks to Dean’s lack of sight and his amazing imagination. Sam arches his back and spreads his thighs and grinds on him like a pornstar, one of his hands sliding up the back of Dean’s neck and up into his hair. “You like m-my tits, Dean? Wanna suck on ‘em?”

“Oh, sweet girl,” Dean groans, his hands slipping down the loose back of his shorts to grip at his ass, hauling Sam forward, deeper into where their bodies are fucking at each other. Dean’s mouth is against his neck, the damp heat of his soft panting  heating Sam up even more, and he full-body shivers when Dean starts to kiss at his neck, at his Adam’s apple and all up and down either side of it, making Sam leak like a whore in his shorts, skin flushed all the way down his shoulders. “I want to suck on ‘em. But I need you to take this off of me first. Let me see how sexy you look before I mess it all up.”

Sam’s passed the point where he’s afraid Dean’s going to laugh at him, so it doesn’t take much prodding for him to reach up and tug the bandana off, Dean’s green eyes bright with hunger and they fly all over Sam, taking in every bit of him presented: the tight pink t-shirt proclaiming Sam a _Princess_ , complete with glittery font and a tiara that is way too small for him and showing off an obscene amount of midriff, his destroyed little denim shorts with holes all in them, so short that the pockets are hanging out at the bottom. His hair is tugged into two tiny pigtails, little sprigs of hair behind both ears, and his lipgloss is cherry-flavored, one that he found left on a desk in class last week and has been sneaking swipes of on his shy mouth ever since.

He lowers his gaze when Dean’s lingers, and he nearly gasps when Dean’s hands slide back up his body, shoving up on his shirt, rough and unrestrained and with a low growl in Dean’s chest.

 “Look so fuckin’ good, baby girl. _Fuck_.” He shoves at Sam’s shirt impatiently, pushing until Sam finally gathers enough brain cells to help, and he rips it over his head, tossing it across the room. Dean’s mouth is on him immediately, kissing down his flat chest as his hands slide up, cupping beneath Sam’s non-existent tits like there’s really something there. “Gonna suck on these sweet little tits. Gonna make ‘em fuckin’ raw so it hurts every time you wear a shirt for a week.”

 “Dean,” Sam whines, not even able to play anymore because he’s mindless, as wanton as Dean always makes him when he gets like this, all hungry, filthy words and bruising hands and a dick that throbs underneath Sam in time with the harsh panting of Dean’s mouth. He sinks both hands into Dean’s hair, guiding his mouth down, down keep going until he’s huffing burning air right over one of Sam’s stiff nipples, and Sam is trembling by the time Dean parts his lips and sucks that nipple up into his mouth, drawing on it hard enough that Sam cries out.

 They’ve talked about it before, about Dean nursing from Sam, about the thought of sucking milk out of Sam’s tiny tits because they’re both fucking perverts and it gets them off. But it feels like Dean’s really trying right now, like he’s starving for it, his mouth insistent and relentless as he sucks.

 “Gimme that milk, baby sister,” Dean murmurs, his voice wet with the spit that’s gathering at the corners of his mouth and thick with lust, and Sam can do nothing but move his hips, riding Dean like he’s got that fat cock inside of him, like he’s working Dean in him with the tight clutch of his teenage ass that is custom-fit for his big brother. The song plays on lewdly from the speakers, like it’s happy to be a soundtrack to their little scene.

 Dean’s got his hands on Sam’s ass again somehow, and he’s pulling Sam in hard as he fucks up against him, both of them racing to an orgasm that will catch them before either of them are ready. Dean pulls back, his lips swollen and deep pink but he only draws in a single breath before he’s latching onto Sam’s other nipple, going in teeth first this time, and the sound that Sam makes is more of a sob than a moan.

 Dean feasts on his breast with careful but sharp bites, chewing on that tender skin until he’s slick with spit and indented and red with teethmarks, the nipple itself an angry, swollen thing, puffed out and stubbornly hard and Sam can only watch as Dean plucks at it with his teeth, as he sinks his teeth into it over and over again.

 “Keep doin’ that, gonna make me come,” he whispers, his dick pressed desperately up against Dean’s stomach, his little ass working overtime on Dean’s cock because he wants them to come at the same time. “Gonna make me come, Dean.”

  _Love is with your brother_

 Dean plays the scene out to the letter, biting down harder on a nipple so raw that it’s nearly bleeding, his breath rushing scalding hot over Sam’s flushed skin, powerful hips fucking up against Sam, both of them still tragically clothed.

 “So fuckin’ sexy, Sammy girl. You’re so fuckin’ sexy.”

 Sam wraps his arms around Dean’s head, cradling him against his chest as he humps hard at Dean’s stomach, his orgasm exploding out of him in thick gushes, Dean’s teeth a searing, painful point of clarity as he falls into it. He feels Dean unloading under him, his whole body jerking hard, thrusting up and up and lifting Sam up off the couch with it, his hands clutching so hard at Sam’s ass he knows there will be long, finger-lines of bruises there tomorrow.

 They curl in together, riding it out as long as they can, muscles tight and hurting but they relax finally, Sam panting against Dean’s ear and Dean kissing across Sam’s chest, lazy and almost apologetic. Sam shudders, drawing Dean up so their mouths can find each other, and he whimpers when his sore nipples press flush against Dean’s cotton t-shirt. Dean grins against his mouth, hands traveling back up Sam’s spine to tug him in tighter.

 “Feel good?”

 Sam blushes, his eyes slipping closed as he nods, and he keeps his mouth soft as Dean kisses him again, letting him suck at the lush thickness of his tongue.

 “Thanks,” he says quietly right against Dean’s lips, arms hugging up around his neck. He doesn’t really want to move for awhile. Dean laughs.

 “Thanks for being as much of a pervert as you? You’re welcome, Sammy. You are so, so fucking welcome.”


End file.
